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Why Sergeant Brewster From Law & Order: Organized Crime Looks So Familiar

The struggle between law enforcement and the mob isn't the only conflict on "Law & Order: Organized Crime."

The New York Police Department is a workplace, and like any other very large workplace, it's filled with people who may or may not like each other, occasionally arcane bureaucratic rules, and turf wars fought by people who are meant to be on the same team. That's part of what Sergeant Bill Brewster brings to "Law & Order: Organized Crime." Brewster is a former boss of Sergeant Ayanna Bell (Danielle Moné Truitt) back when she worked in Narcotics, so the idea of heading a task force together, as the pair are asked to do in the show's second season, sees him struggling with the notion of treating her as an equal. It may not be the showiest bit of intra-department drama on the series, but it's a major test for Bell. 

You don't have to go far from "Organized Crime" to find some of actor Guillermo Díaz's work before he was cast as Brewster. He's done two different episodes of "Law & Order" and two episodes of "Law & Order: Special Victims Unit" as well. From starring in a pioneering LGBTQ drama to cult classic comedies to one of the biggest television sensations of the last decade, Díaz has assembled an impressively varied resume. Here are some of the places you might recognize him from.

Guillermo Díaz played a guide to Stonewall

Díaz landed his first appearance on the flagship "Law & Order" just as he was starting out in 1994. He also appeared that year in the crime drama "Fresh," and in 1995 played struggling roommate Leo in the Parker Posey-starring "Party Girl."

But it was in 1995's "Stonewall" that Díaz had his biggest early role. Díaz played the drag queen La Miranda, who shows newcomer Matty Dean (Frederick Weller) around the Stonewall Inn and the rest of New York City's LGBTQ scene in the weeks leading up to the Stonewall riots in the summer of 1969. Matty drifts back and forth between La Miranda's showy defiance of convention and the more muted conformity of the activist Ethan (Brendan Corbalis). In the end, he chooses La Miranda, and the film ends with the police raid that touches off the riots.

In an interview with The Daily Beast given ahead of the 50th anniversary of the Stonewall riots in 2019, Díaz said that even though he grew up in New York City, he hardly knew anything about the Stonewall riots until he went to college. Working on the film, he said, gave him a new perspective on how crucial that generation's fight was. "It gave me a sense of community and a wonderful feeling of pride and respect for all those who were there and sacrificed SO much for the LGBTQ community," Díaz told The Daily Beast. "I just remember feeling REALLY proud to be gay."

Guillermo Díaz brought Scarface to Half Baked

In 1998, Díaz was cast as one of four stoner roommates in Dave Chappelle's cult classic comedy "Half Baked."

Díaz played Scarface, who joins the scheme of his buddies Thurgood (Chappelle) and Brian (Jim Breuer) to sell medical marijuana in order to bail out their friend Kenny (Harland Williams) from prison. "Half Baked" found little early success with critics or audiences, making just $17 million at the box office, but Díaz got one of its more oft-quoted moments when he quits his job at the fast-food restaurant His Royal Beefiness. He hops on the intercom and curses out his co-workers one-by-one, but interrupts the series of expletives he's delivering to each of them in turn in order to tell a customer, "You're cool."

It would prove worth it for Díaz. He told Conan O'Brien that his experience on set was "the most fun I've ever had making a movie," for reasons you might be able to predict. Collaborating with Chappelle would also pay off down the line for Díaz, as he was a regular guest star on the comedian's Comedy Central breakout "Chappelle's Show," including a few appearances as Scarface.

Guillermo Díaz kept coming back on Weeds

In 2007, Díaz took a role on a different sort of marijuana-themed project, the Showtime comedy-drama "Weeds."

Díaz played Guillermo García Gómez, a mid-level gang leader in the Tres Seis criminal organization introduced in the show's third season. His work brings him into contact with suburban dealer Nancy Botwin (Mary-Louise Parker), who offers him money in exchange for his and his associates' protection. That begins a tumultuous relationship, with the pair exchanging threats and blackmail attempts and Nancy selling him out to the DEA even as she and his boss, Esteban Reyes (Demián Bichir) become romantically involved. Despite their back-and-forths, the pair eventually find a way to work together in the show's eighth and final season.

Díaz admits to having some nerves joining a cast with that kind of reputation a few seasons in, but he told MovieWeb his co-stars, particularly Parker, helped ease him in. "She's so good and so there and so sweet," he said. "I feel so lucky to be able to act with all these people who are really seasoned actors. It's just been like a dream, man."

Guillermo Díaz played an Ángel on Mercy

"Weeds" was far from Díaz's only role as a gangster. He played one in the Jon Lovitz comedy "High School High," the Kiefer Sutherland and Reese Witherspoon dark comedy "Freeway," and in 2010's Bruce Willis and Tracy Morgan buddy comedy "Cop Out." But in 2009, he went back to his "Stonewall" roots to play the out-and-proud nurse Ángel García on NBC's medical drama "Mercy."

"I was starting to feel like I was just playing the bad guy," Díaz told Out Magazine. "I was ready to queen out a bit." Switching between those types of roles comes naturally for Díaz, he explained to Out, because of his upbringing. "'I went to school in the Bronx," he said in that interview. "I learned to constantly try to cover up the fact that I was gay. That facade of being somebody I'm really not just to protect myself definitely helped with acting."

But as he explained, his early management thought he'd get more work if he steered in the direction of criminal parts and kept quiet about his sexuality. He left them behind, and so was able to move back and forth between different kinds of parts on his own terms; "Weeds" on one side, "Mercy," at least for its short run, on the other. "It's never been an issue," he said. "I've worked constantly."

Guillermo Díaz was cold-blooded on Scandal

In 2012, Díaz took on what may be his most recognizable role yet, playing Olivia Pope's (Kerry Washington) tech and torture whiz Huck on ABC's political thriller "Scandal." A Marine veteran and former assassin for the show's top-secret clandestine organization B613, Huck presents a pretty severe personality throughout most of his time on the show. He's willing to do anything to help Olivia Pope & Associates in their work, but he's also haunted by some of the things he has done, and his own penchant for enjoying them.

As Díaz tells it, his time on "Scandal" definitely introduced him to new audiences, people who might be surprised to learn his background. "I've done like a million comedies, and now I did 'Scandal' and whenever I smile around people they're like 'Ohh my God, you smile.' And I'm like 'I've been smiling for years," he told Ellen DeGeneres and Rob Lowe on "Ellen."

But just because his personality doesn't match Huck's dour demeanor doesn't mean he didn't enjoy playing such roles. "I get so excited when I have to do torture scenes," he told Steve Harvey on his talk show. "I'm a huge horror film fan," he explained, backing up why the chance to play someone's horror villain for the day was thrilling for him.